1,2-Dichloroethane → 4-Ethynylbenzoyl-2(S)-phenylsulfonylamino-beta-alanine ethyl ester

HRID 583711

Reaktionsgleichung

Reaktionsgleichung von HRID 583711
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1)#[CH:2].[C:12]1(C)C=CC(S(O)(=O)=O)=C[CH:13]=1.C([NH:25][CH2:26][C@H:27]([NH:31][S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:34])=[O:33])[C:28]([OH:30])=[O:29])C.CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[CH2:12]([O:30][C:28](=[O:29])[C@@H:27]([NH:31][S:32]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)(=[O:33])=[O:34])[CH2:26][NH:25][C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([C:1]#[CH:2])=[CH:11][CH:10]=1)[CH3:13]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 5897064-Ethynylbenzoic acidHCID 86752459Ethyl 2(S)-phenylsulfonylamino-beta-alanine p-toluenesulfonate

Produkt 1

HCID 867524584-Ethynylbenzoyl-2(S)-phenylsulfonylamino-beta-alanine ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Ethynylbenzoic acid (35-1) (3.10 g, 21.2 mmol), 35-2 (8.58 g, 19.3 mmol), NMM (8.49 mL, 7.72 mmol), HOBT (3.39 g, 25.1 mmol), and EDC (4.81 g, 25.1 mmol) were combined in 96 mL DMF and stirred overnight. The reaction was concentrated, residue was diluted with EtOAc and washed with water (2×) and brine, dried (Na2SO4), filtered, and concentrated. Flash chromatography (silica, 45-50% EtOAc/Hexane) gave 35-3 as a white solid.

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. additionresidue was diluted with EtOAc
  3. washwashed with water (2×) and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-268a8eabed7640b0a9ec915cc4429c22
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05929120

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